Second Time Lucky
by sistervamp
Summary: Yellow Eyed Demon is gone. John is dead. And somehow Dean now has a 5 month old baby boy instead of an gigantor of a 23 year old brother. What will he do? Told in a series of flashbacks. Rated M mostly for the use of foul language.
1. Dear Son: The Prologue

**A/N: So probably best to describe the set up just in case it confuses anyone. The story is basically the ramblings of a dying man and he's remembering instances in any old random order and since he wrote them down as soon as he remembered them, so they will be uploaded accordingly. So I thought I'd start with the letter to set the scene for the rest of the story. Anyway here's a detailed Summary although it begins to make sense as the early memories of 27 year old Dean come into it: Sam and Dean were able to stop the YED, but Sam became de-aged and was to have no memory of the hunting life whatsoever, Dean had to raise him again and make some new decisions. One being that he would become the now baby!Sam's father. _  
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**So on to the formalities. I do not own any of the supernatural characters, I however do own Robert Steven Winchester (No matter how much like the older Bobby he seems), Jasmine, Katherine and Jacqueline.**

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_Dear Son, _

_If you're reading this, then I've died. Don't be too upset, it's not the end of the world, I've seen enough to know that there's a flip side. When I came to be your primary carer at 27 I was quite honestly terrified. I remember freaking out and simply running to the woman who I knew could help me, she had always had that maternal instinct, she was like the real world version of Monica, a mother without a child. I'd expected her to be married with at least one kid, but I was only half right, she had the child, but no husband. Turns out his father was a deadbeat and quite honestly the sort of guy that I wanted to wring his neck for leaving her to raise the kid alone. To be fair to the woman, she'd done an amazing job with raising the boy. It's thanks to her that I became the father I did, behind every good man there's an even better woman, remember that. _

_I knew I was dying a few months ago, I was more tired and I just knew it was time for me to be going soon. I decided to write down everything I could remember about me raising you, even right through your bratty teenage years, perhaps in small part so you know how to deal with it with your own son. That's another thing, the Colt 1911, MY colt 1911, it's yours, keep it away from your son though, I still remember when you stole it that time, how could I ever forget? You were never a bad kid, just hard to handle sometimes. Thing is, I remember worse arguments between my father and younger brother, although to be fair John Winchester was a dick even if he managed to get my record cleared and have it put down as a mistake. If any of what you learned about me and also yourself really makes no sense, please find Chuck Shurley, he's still probably hiding under the name of Carver Edlund. I swear kiddo, you had better find him or I will haunt your ass!_

_When Ben's away look after the girls and Bobby. I still can't believe your sister had a little boy that had the infamous Robert Steven Singer patented scowl at birth and for the love of all that is vaguely holy, make sure Ben doesn't find his father and put a bullet in him. Like I told the kid, the Jerk isn't worth the jail time, but you know how stubborn the guy is. He did make it to staff sergeant after all, not entirely sure if that's stubbornness or stupidity, probably both to be frank with you._

_Always your dad, _

_Dean John Winchester (Yes I still detest that damned middle name)_


	2. Sam And Dean's Colt:Chapter 1

Sam was playing up, he was on a collision course for disaster. Every year as Sam got older, the more Dean hoped and actually prayed that this would be the year that Sam turned a corner and stopped his stupid behaviour. He understood that his son had been close to Bobby Singer, but so had he and it was hurting the family to see Sam so dangerously close to finally losing his mind or life. He had been eleven then and it had started with the odd shoplifting incident, but then it had escalated to joy riding and by the time Sam was sixteen, Dean was starting to expect a phone call from the police informing him that his son was dead or in prison. So when the doorbell went, he was resigned that his 16 year old son was in deep trouble, how many more times would he have to discipline the kid? It wasn't working and he was certain one day his heart would give out from the stress. He opened the door to see his 16 year old son and a bunch of other kids that he recognised as Sam's friends with the old man from up the road.

"What can I do for you Burt?" Dean asked trying not to throttle his son.

"This lot were on my land shooting at beer cans and smoking." Burt explained with ire in his voice and honestly Dean couldn't blame him.

"That right?" He raised an eyebrow, so perhaps it was a bad idea to teach the kid how to shoot and to leave that damn Colt 1911 about, actually that was a point, why had he left it out?

"Yeah. Take your boy and deal with him, but be warned if he's on my property again I will shoot him." Burt growled as Sam finally registered fear.

"Samuel Winchester get inside before I drag you in!" Dean demanded extremely annoyed. Sam of course refused to move but he didn't get smart either so his father just dragged him inside with an apology to Burt and sending the other boys home. Once the door was closed Dean turned to his son full of rage and glared.

"You took my gun, you trespassed and you're smoking? You're going to end up dead one day soon if you don't stop this." He lectured Sam, it wouldn't be long before he began to full on lecture him, the last time that had happened Sam's ears didn't stop ringing for two days, or perhaps that was his mother boxing his ears that did that.

"Like you care dad. The only guy who's ever cared is dead so yeah so fucking sorry for not listening to your shit, but you may as well have been a sperm donor, remember it takes someone damn special to be a dad and someone even more special to be a great dad." Sam snapped his fists clenched and his jaw set, just like his uncle did at that age and that thought sent a pang through Dean's heart.

"Of course I care, you have no idea what I've done for you, how your life could have turned out. Bobby's been dead five years son, move on. I know it hurts, the man was like a father to me, hell he raised me, but that does not excuse your behaviour. Tomorrow you will apologise to Burt and for goodness sake sort yourself out before you get arrested or die, you won't be going to college otherwise. Book your ideas up son!" Dean lectured finally snapping and beginning to yell, that was never a good sign.

"Mind your blood pressure dad. I'm off to see Jasmine if you don't mind." Sam shrugged almost laughing, he really couldn't care less anymore and before Dean could stop him, the youngster grabbed the keys from the counter and jumped into the impala driving off. Sam Winchester would be the death of him one day.

Dean shook his head as he pulled out a bottle of beer from the fridge, flipping the top off with his hand. He was so wrapped up in his own thoughts that he hadn't heard his eldest walk into the room, despite the fact he used to joke that with all those damn brain cells rattling around in the kid's head he should be able to hear him. After all what idiot willingly joins up for the airforce? Oh that's right, Benjamin Issac Braeden._  
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"Sam playing up again?" Ben asked as he handed the man he'd grown to respect like a father, the newspaper. Ever since the death of the family matriarch when he'd been 18 had been hard on everyone, the girls coped, especially with the help of Jasmine who'd lost her father that very year. He was ever so thankful that the girls had someone there for them, even if it was the crazy girl next door. The girls were managing, but Sam wasn't, first Bobby and now their mother? How could he come back from this?

"Playing up? Ben, he's being a complete ass. Sammy was never this bad growing up, sure he had his moments, but they were usually sorted out by him going off to school and Dad deciding we had to move again. Why is Sam being so difficult?" He sighed as she chugged down his beer. It was the first beer he'd drank in 7 months, in fact it was the first drop of alcohol he'd had in as long and it didn't bother him at all. He differentiated between the Sam that had been his brother and the one who was his son by calling his brother Sammy and his son Sam. Ben knew the story, especially after what happened with the changelings, thank goodness they'd only gone after 8 year olds and not babies. That would have just made things difficult with Sam being one at the time and the twins barely a couple of months old.

"Sammy was used to death and coped differently, but Sam isn't. He and Bobby were close, he saw the cranky guy as his father figure, despite the fact he had an amazing one right here. Even I look up to you as a dad. As a kid I always wanted you to adopt me as your son, I guess thinking about it now, you've always been my dad, even if you're not my father." Ben smiled, he remembered that final conversation with his mother, it was obvious in his eyes. Those brooding eyes that he'd inherited off his mom. Dean never spoke it out loud, but he didn't need to, he'd have been dead proud to have been Ben's father, but as his dad, he already was proud. Then again, perhpas that was what Sam's problem was, he was jealous of Ben.


End file.
